Conservatives have a problem with cool. If they were smart, right-wing pundits and Republican political consultants would just ignore the whole concept of cool. Being conservative is inherently uncool, since the whole point of conservatism is to reject the forward-looking and liberated attitude that has always defined cool. Worrying much about it is just a waste of time. Trying to be cool just makes you look ridiculous, and paradoxically, more uncool. It’s a no-win situation, and yet conservatives continue taking the bait, forever trying to get this whole concept of cool to work for them and always, always failing.The latest example of the Republicans trying to figure out to work this cool thing and failing is an ad campaign running in 14 states with Senate campaigns in 2014 that shows Scott Greenberg, a 30-year-old Audi driver saying things like he is “ticked off at politicians” for passing regulations, which he believes are the source of unemployment. We are clearly meant to believe that Greenberg is a hipster, demonstrating the infallible conservative ability to hop on any trend right after it’s run out of steam. Greenberg wears a striped shirt and glasses and has a scraggly beard, but sadly for Scott Greenberg and his benefactors, none of that does much to conceal the eau de dweeb that hovers over anyone who takes seriously the idea that wealthy businessmen are the major oppressed class of America.It’s hard to see why Republicans even bother. Even if it were possible to trick young voters into thinking you can vote Republican and still be cool, it isn’t really necessary. It’s not like the millennial crowd is dweeb-free, for one thing. For another, the usual tactics of using catchphrases like “small government” and “personal responsibility” to cover up race-baiting pandering to white people is working pretty well on white millennials, though perhaps not quite as well as it did on white people before.No, it’s safe to say that this attempt to be cool is less about really peeling off votes from the Democrats. No, this is about something deeper, a long-standing jealousy and resentment of the left for being a giant vacuum that sucks up all the cool people, leaving behind the right. (Let’s be clear, by no means am I saying all Democrats are cool. They have their fair share of dorks and dweebs. But it is, and many Republicans are keenly aware of this, true that most cool people are pretty liberal. It just comes with the territory.) This creates a major insecurity on the right, and periodically there are embarrassing attempts to deal with it by asserting, laughably, that they have cool people on their side of the aisle, too. It’s painful to watch.The “nuh-uh, we’re cool, too!” thing has a long and sordid history on the right. Take Andrew Sullivan’s embarrassing attempt to coin the phrase “South Park Republican” in 2001, to describe the younger and cooler form of Republican that was supposedly emerging at the time, and was characterized by being into the show South Park, or at least the worst part of the show, which was its tendency to devolve into half-baked reactionary moralizing from the perspective of writers who clearly didn’t understand the issues. Even the conservative website Daily Caller had to admit recently that “South Park Republicans” had no traction, calling them the “political equivalent of a dodo bird,” which is overgenerous. Roy Edroso more correctly called it more of a fantasy than a reality, pointing out that even at its strongest, South Park Republicanism was straight-laced and more concerned with policing “morality” than letting loose and having fun.It’s the same urge that, among the Christian right, leads to Christian rock and churches like Mars Hill in Seattle, where the pastor attempts to fool you into thinking he’s cool because he rocks a beard and likes rock music, but you find out at the end of the day, he’s just selling the same old fundamentalism as the more buttoned-up crew.This is a more secular version of the same urge, and frequently leads to conservatives identifying as “libertarian” without having any meaningful policy differences from the same old Republicans of yore. In the media, it leads to unconvincing attempts to craft hip, bold, young conservative voices—like S.E. Cupp or Greg Gutfeld—that don’t really seem to be fooling anyone except the cranky old conservative audience that can’t really tell the difference. (Gutfeld, at least, has decided to embrace his lack of cool, writing a new book called Not Cool: The Hipster Elite and Their War On You, where he takes another tack of trying to pretend that he wasn’t into that whole “cool” thing anyway.)But where these attempts to make conservative cool reliably come across as the most pathetic is in the realm of rock music, the great white whale of the right. Conservatives, particularly Baby Boomers, have never really gotten over the fact that they were on the wrong side of the ’60s. Witness the insistence on calling CPAC—or the Bakersfield conference or the Tea Party—“Woodstock for conservatives.” Woodstock happened 45 years ago, and clearly the right is still upset that they weren’t a part of it. This, too, explains how, no matter how outrageous or racist or sexually predatory Ted Nugent gets, Republicans can’t let him go or stop using him in fundraising. He’s a rock-and-roller, really the only one they’ve got, so they’re clinging to him like a barnacle on a sinking ship. The only other option is pulling a Chris Christie and following Bruce Springsteen around, trying to make him validate you even though he’s clearly not having it. (Witness the saddest non-serious headline in possibly all of the 21st century: “Chris Christie hopes Bruce Springsteen will be his friend someday.”)If conservatives were smart, they’d simply ignore cool altogether and go golfing and spend money and simply give up any hope of being cool whatsoever. That strategy of indifference worked for Ronald Reagan. Say what you will about him, he seemed perfectly content to be himself in all his utterly out-of-touch glory, and he was all the more popular for it. The current strategy of being all hung up about it, and desperately casting around for something, anything, that shows that Republicans can be cool, too, only ends up backfiring. After all, nothing is less cool than trying too hard to be cool, and failing.

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